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Men's Style With Boots: Outfit Ideas for Leather Boots

The idea that boots aren't for men is insane. Before there were women's boots, there were men's boots. They were first in both utility and fashion.

Utility first in that they were for fieldwork and horseback riding. then fashion when it came to royal courtesans.

But you're not going to wear boots the way that the French royal court did. That's way too many ruffles to put up with.

So how will you work your style with boots? Read about the types of men's boots and how to put outfits together with them below.


Men's Style with Boots - Helm


Types of Men's Boots: The Chelsea

The Chelsea boot is a classic slip-on boot, with a low profile that can work as a dress shoe, or something a little more casual. It's not something you'd wear to a backyard bbq, but you could wear one out to a three or four-star dinner.

They work with your suits or dress pants for work as well, as long as you're wearing them in a dark neutral.

For more formal or fun-dressy occasions, look for a boot in a velvet material or loud color.

Capped Toe Dress Boots

Another option to wear out to parties or to work is the capped toe dress boot. It has a classic lace-up top, as you'd see on athletic shoes, but classed up.

The laces blend in with the color of the shoe and aren't necessarily functional. They may help keep them on your feet, but they won't tighten them a full size down or anything like that.

They're great for rustic-themed weddings or with your darkest pair of denim jeans.

The darker the color you get the boots in, the more formal they'll look, so keep that in mind.

Wingtip Boots

What's a wingtip brogue boot vs a capped toe boot? The wingtip has more of a design on the toe. It's also a little bit longer than another boot of the same size, a little bit like a women's pointed toe shoe (but much more subtle).

Most wingtip boots are in a light to dark brown leather. They come in black, but it's harder to see the detail on the tips.

They have the same sort of leather lace-up as the capped toe boots, and you can wear them at the same locations. Just know that lighter leather is less formal than darker colors.

Ankle Boot

If you're manly enough to rock a slight heel on a boot (and no, it's not a high heel, it's chunky and low). Then you should go for this boot.

It's based on a classic man's riding boot, which is why it has a heel. In horseback riding, the heel would rest in the stirrups.

They look great with tapered denim or chinos, or even the more fashion-trending waxed jean trend.

The darker the boot, the easier it is to pull off the slight heel.

Chukka Boots

If you're more of a casual-type guy, try wearing Chukka boots out with friends. They're a casual ankle boot with a short tie - it only laces through two or three times.

They're the most casual of all the boots on this guide and usually come in a lighter color leather or suede.

Cowboy Boots

Did we say Chukka boots were the most casual? A cowboy boot can be casual in some parts of the country. The parts where, you know, people actually need cowboy boots for work reasons.

Otherwise, you're looking at dress boots, which are best left a country bar or concert. Or a rodeo - if you're riding in it.


Men's Style Tips with Leather Boots - Helm Boots


Your Style With Boots: How to Rock Each Type in Different Outfits

When you're going out on the town, going to work, or going to an event, you want to look your best. Here's how to do that.

Smart Casual Outfit One: The Chelsea Boot

If you have a Chelsea boot you're wanting to wear. get a pair of dark straight jeans. Not skinny jeans that cling to your legs, but straight jeans that don't give too much volume in the ankle.

That will keep the jeans from overpowering and hiding the boots. No matter what color your boots are, go for a dark wash of jeans. Lighter washes are more casual and, if we may, more outdated.

Pair this with a smart black shirt, french tucked into your jeans.

This outfit will get you from dinner with your work friends, to drinks with your date, even to meet the parents at a reasonably nice restaurant.

Semi-Formal Outfit One: The Chelsea Boot

If you want to dress up your Chelsea boot, then you should go for something unique in color or texture. Like velvet or a bright leather that demands attention.

Pair that with a regular suit and tie, but skip the full shirt tuck in. Do the French tuck thing, which means you only tuck in the part of your shirt so that you can (essentially) see your belt buckle.

Or where the belt buckle will go. A French tuck is a good marriage between "I'm trying to get a raise" formal and a normal day at work.

It's also slimming if that's something that interests you. If you want to learn more about the benefits of the French tuck, watch the second or third season of Queer Eye for the Straight Guy on Netflix.

Fashion mogul Tan France is a big fan!

Semi-Formal Outfit 2: Capped Toe Boots

If you need something a little more formal, then you go with a capped toe dress boot. The detail on the boot and the shine of the leather finish take it from night out with friends, to a night out with your boss.

To wear them, consider the color leather you have. Some people have a problem wearing brown and black. Brown shoes and black pants. Others don't.

We're neutral on the black/brown matter (get it?) Brown shoes look great with navy pants if you're in the anti camp.

Once you have your coordinating color dress pants on, pair them with a colorful pair of socks. Colorful socks are the power move since if you cross your leg at your knees in a meeting, the pop of color will just peek out.

Dress your top half as you would for any other semi-formal event, with a dress shirt or even a suit jacket.

Smart Casual Outfit 2: The Wingtip Boot

Wingtips are classically formal shoes, but we love how they look with a nice, dark pair of jeans. A tan leather boot contrasting the dark denim is the way to go.

You can pair this outfit with about anything on top, but we recommend a casual button-down shirt, with some cool pattern on it.

We're seeing kitsch all over the runways this year, which basically means something a little cheesy and bright. A white short sleeve button down shirt with a design of bananas spaced every couple of inches, for example.

This mix of playful and classical will make you the most stylish man in whatever room you walk into.

Semi-Formal Outfit 2: Wingtip Boots

If you want to wear your wingtip boots as work or dress shoe, the same black/brown rule applies. You have to make your own decision on that front.

Better yet, get one pair of black and one pair of brown. Then you have something that goes with everything and you don't have to worry about what to wear with what.

Put on your dress pants, and make sure they're well-tailored so that they stop right at your ankle bone. That should give the shoe a good amount of room to shine, but it shouldn't make the pants bunch up around the ankle.

Pair it with a colored dress shirt, something that pops, especially if you're wearing a matching suit jacket. Or go for a bright but plain-colored tie, to give your outfit some visual interest.

Your Style With Boots

Now that you have a better idea of how to rock a mans' style with boots, you should start checking out what you have in your closet. Maybe that means throwing away those old, faded jeans that you've had for ten years.

Upgrade to a more grown-up dark denim and have them professionally fitted/tailored. That's going to make whatever boot you wear look like a rockstar.

If you're low in the boot department, or maybe have never worn one - you can shop our selection here. We only use premium materials and you'll be in love at first step.


To pick up your next pair of black ankle boots, visit Helm Boots. We're an Austin-based bootmaker that specializes in high-quality, good-looking, and affordable boots for every look.


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